Potassium Phosphate, Tribasic → 4-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide

HRID 1178977노트

반응식

HRID 1178977 반응식
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][NH:7][C:8](=[O:28])[C:9]2[CH:14]=[CH:13][C:12]([S:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20](I)=[CH:19]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH:31]1(B(O)O)[CH2:33][CH2:32]1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([C:20]2[C:21]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]([S:15]([C:12]3[CH:13]=[CH:14][C:9]([C:8]([NH:7][CH2:6][C:5]4[CH:29]=[CH:30][C:2]([F:1])=[CH:3][CH:4]=4)=[O:28])=[CH:10][CH:11]=3)(=[O:17])=[O:16])[CH:19]=2)[CH2:33][CH2:32]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 58975061N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide

생성물 1

HCID 589750114-(3-Cyclopropyl-indole-1-sulfonyl)-N-(4-fluoro-benzyl)-benzamide수율 60%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

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온도
100 °C

실험 절차

Combine N-(4-fluoro-benzyl)-4-(3-iodo-indole-1-sulfonyl)-benzamide (0.50 g, 0.94 mmol), cyclopropylboronic acid (0.24 g, 2.8 mmol), tricyclohexylphosphine (0.05 g, 0.18 mmol), potassium phosphate (0.70 g, 3.30 mmol), and palladium acetate (0.02 g, 0.09 mmol) in a mixture of toluene (15 mL) and water (0.4 mL). Heat to 100° C. under nitrogen for 18 hours, filter through celite, and wash solids with EtOAc. Wash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4, and concentrate under vacuum. Purify by flash column on silica gel eluting with 0-50% EtOAc in hexanes to give the title compound (0.25 g, 60%). MS (ES) 449.2 (M+1)+, 447.4 (M−1)−.

후처리

  1. filtrationfilter through celite
  2. washwash solids with EtOAc
  3. dry with materialWash EtOAc with saturated NaHCO3 (30 mL), then dry with Na2SO4
  4. concentrationconcentrate under vacuum
  5. customPurify by flash column on silica gel eluting with 0-50% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-f07dbabf5c5547138b6ced4349f08f3a
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276516B2

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